...and he did, in Superman's Pal Jimmy Olsen #23 (September, 1957), under this cover by Curt Swan and Ray Burnley!
The Adventures Of Private Olsen
Here, in this tale by Otto Binder, Curt Swan and Ray Burnley, Jimmy goes on a story for the Daily Planet, to find out what it's like to be in the army, getting a little help from Superman and his friend, Colonel Otis. Going undercover as Private Hudson, Sgt. Blye decides to make a little money off the boy, by betting he'd fail, but also hedging his bet by making everyone else think he's a general's son, who would be a natural soldier.
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